Having come through the youth academy at Manchester United, he spent time on loan with Huddersfield Town, Cardiff City, Watford and Barnsley.

After moving to Chelsea in 2017 and making few appearances for the London-based club, he spent the remainder of his career on loan at Burnley, Aston Villa, Kasımpaşa and Reading.

[5] In the 2008 Lancashire Senior Cup final against Liverpool on 31 July 2008, he came on as a 56th-minute substitute for Rodrigo Possebon before scoring the winning goal three minutes from full-time.

[5] At the end of the season, he was called up to the Manchester United first team for their dead rubber league match against Hull City on 24 May 2009.

[7] To gain first-team experience, on 14 August 2009, Drinkwater joined Huddersfield Town on loan for the duration of the 2009–10 season.

[15] Just three days after his return to Manchester United, Drinkwater joined Watford on 28 January 2011 on loan until the end of the season.

[24] On 17 June 2014, he signed a new four-year deal with Leicester after helping the Foxes win promotion to the Premier League for the first time in ten years.

[25] Drinkwater played consistently as the Foxes won the Premier League title in 2015–16, alongside his midfield partners N'Golo Kanté, Marc Albrighton and Riyad Mahrez.

[30] Due to a thigh injury that ruled him out previously, he made his debut on 25 October in the last 16 of the EFL Cup, playing an hour of a 2–1 home win over Everton.

[41] Aston Villa manager Dean Smith watched Drinkwater train with the team before confirming his loan deal.

Smith stated that he was confident that Drinkwater had put the issues that had affected his previous loan behind him and he would be ready to provide cover for the injured John McGinn.

In an interview with The Telegraph in September 2020, he spoke of his off-field issues and stated his desire to get his career back on track, including the possibility of playing abroad.

[55] Drinkwater was named in Roy Hodgson's 26-man provisional squad for UEFA Euro 2016 but was one of three players axed for the final selection.

[57] In September 2019, Drinkwater was attacked outside a Manchester nightclub, allegedly following a dispute with fellow footballer Kgosi Ntlhe, which resulted in ankle ligament damage.